


Dear Hopeless

by i_took_the_sense_of_humor_in_the_divorce



Category: Carry On Series - Rainbow Rowell, Simon Snow & Related Fandoms
Genre: Agatha unknowingly gets snowbaz together, Alternate Universe, Alternate Universe - Canon Divergence, Asexual Agatha Wellbelove, Enemies to Friends to Lovers, M/M, POV Agatha Wellbelove, Relationship Advice, Watford Eighth Year, advice column AU, anonymous letters, getting together (outside pov)
Language: English
Status: Completed
Published: 2020-12-14
Updated: 2021-02-09
Packaged: 2021-03-11 04:54:35
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 3,977
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28059522
Author URL: https://archiveofourown.org/users/i_took_the_sense_of_humor_in_the_divorce/pseuds/i_took_the_sense_of_humor_in_the_divorce
Summary: AU where Agatha runs an anonymous advice column in Watford’s school paper
Relationships: Penelope Bunce & Agatha Wellbelove, Penelope Bunce & Simon Snow, Simon Snow & Agatha Wellbelove, Tyrannus Basilton "Baz" Pitch & Agatha Wellbelove, Tyrannus Basilton "Baz" Pitch/Simon Snow
Comments: 16
Kudos: 120





	1. A Wax Sealed Letter of Lament

**Agatha**

I opened the little brass letter box and collected the daily submissions. It’s a standard procedure by now, but I still find it exciting each time. I keep hoping I’ll find a particularly interesting submission, but I never do. It’s always the same stuff- fights between friends, fishing for compliments, vague life advice…

I flip through the letters, they’re mostly just short messages scrawled on loose-leaf paper- probably scribbled in the middle of class.

Except for one.

  
My fingers trace the gold embossed envelope carefully. I’ve never gotten a submission this formal before. It has a wax seal on the back, keeping the envelope sealed tightly. I’ve never gotten a submission this carefully packaged, either.

Interesting.

I tuck the letters into my coat pocket and lock the little brass box once again.

It’s rather cold out, but I’m careful not to crush the letters in my jacket as I head back to my room.

I sit down at my desk and carefully peel back the wax seal, pulling the letter from within the fancy envelope. It’s written on _stationary_. Someone is taking this very seriously.

_Dear Miss Everything,_

_I have a problem. I’ve developed feelings for someone. The issue is, they hate me. I don’t know what to do. I’ve known how I’ve felt for several years. I keep hoping I’ll just get over them, but it seems my feelings only grow stronger by the day._

_Is there anything that you think I can do to fix better my situation?_

_Sincerely,_

_Hopeless_

_P.S. I’d rather not have this published. I placed a rock next to the willow tree on the eastern side of the Weeping Tower. If you are going to respond, please leave your answer under the rock._

Well that’s something new. I don’t think I’ve ever gotten a letter like this before. I’ve certainly never gotten one asking not to be published (or one that’s asked me to place a response under a rock).

I wonder who wrote it… The handwriting looks familiar, but it’s so neat and nondescript that it’s hard to say whether or not I’ve ever actually seen it before.

I grab my typewriter and start to formulate my response.

_Dear Hopeless,_

Right. That’s the only thing I can come up with. What am I supposed to tell this person?

_Don’t be scared to shoot your shot! You may think that they hate you, but it’s always worth a try! If you want things to change between you, then you have to be the one responsible for that change!_

_Try getting along with them! Give them compliments! You can start out with very general compliments, but as you two start to get along better you should switch to more specific compliments. Don’t immediately start acting like you’re super interested, though. Ease into it slowly, relationships and trust take time to build._

_Sincerely,_

_Miss Everything_

That should do it.

I put my coat back on and make my way over to the Weeping Tower. Sure enough, there was a rock at the foot of the willow tree on the eastern side of the tower. It was only about the size of an orange, and I got dirt on my hand when I slipped my carefully folded response under it.

I hope that whoever “Hopeless” is, they find my response. I hope they manage to fix their love life. Merlin knows I shouldn’t be the one giving them relationship advice.

It’s been a few weeks since Simon and I broke up. I have to say, I made the right decision in ending it. We just weren’t right together. I don’t know if I ever really loved him in that way, but I can say for certain I didn’t by the end.

I spot Baz walking across the courtyard and wave to him, which he either doesn’t notice or ignores (probably the latter). Deep down, I know what Baz said was true, we are wrong for each other. I can’t tell if I like him, the idea of him, or just what he represents. Not that it really matters, he’s made it clear he’s not really interested.

I shrug off my coat and sit back down at my desk, flipping through the letters once more.


	2. A Loose-Leaf Letter of Skepticism

**Agatha**

It’s been four days since I got Hopeless’ letter, and we’ve been talking regularly. It’s a bit of a strange routine, if I’m being honest, but I’m starting to enjoy it!

I’ve never gotten a reoccurring letter writer before. This advice column isn’t really taken seriously, even by me. I mostly started it so I could have some non-athletic extra curriculars on my transcript, but it is somewhat enjoyable.

Every morning I check the letter box before breakfast, and Hopeless has left a new letter every time. I read their letter during breakfast and write my response during Magic Words class. I leave my response by the willow tree during lunch, and I assume they pick it up around dinner time.

So far, I think I’ve underestimated just how delicate the situation between Hopeless and their person of interest. The more they reveal, the more the odds seem stacked against them. This was their last letter:

_Dear Miss Everything,_

_I appreciate your advice, but I think I may need something more specific. I understand you’re working with very limited information, but I’d rather maintain my anonymity, so I can’t tell you much more about the situation without giving away my identity._

_I suppose the main issue is that I haven’t made it difficult for them to hate me. I can’t fully wrap my head around why I do it, but it seems impossible to stop. The two of us are constantly at each other’s throats. Every time I open my mouth I only make things worse, it’s almost a reflex at this point._

_To make the situation worse, they think I’m constantly trying to plot against them (it’s ridiculous, really). Even as I’m sitting at my desk writing back to you, they’re accusing me of devising their downfall. How can I get them to trust me when they think I’m rooting for their downfall? Is this as lost a cause as I think it is? I need a second opinion from someone not so closely involved in the situation (or anyone besides myself)._

_Sincerely,_

_Hopeless_

I mean, really, this person knows even less about handling romance than _I_ do (and that’s saying something)! I suppose I should tell them as such…

_Dear Hopeless,_

_I can say for certain that the first step to winning your person-of-interest’s heart is to start being civil with them. Don’t start with outright niceties, they might be suspicious if you act pleasant out of nowhere! Try avoiding conflict with them as much as possible. Once it starts to come naturally, you can try going slightly out of your way to be nicer to them. Remember: BABY STEPS!!! _

_You don’t want to rush this. If you want their trust, you need to establish trustworthiness over an extended period of time._

_I know hopelessness is kind of your whole theme (hence the pen name), but I’ll be honest with you… I don’t think it’s as impossible as you seem to believe. You say they hate you, but being able to rile them up enough to get a reaction is a sign that you’re an important factor in their life (as morbid as I know that sounds, trust me it’s not a bad thing)._

_Let me know how it goes!_

_Miss Everything_

_P.S. I refuse to take responsibility for how any of this goes, use my advice at your own risk._

* * *

I open the brass letter box but there’s no reply. I guess that was the end of it. I close the lid again, but something catches in the side, sticking up awkwardly. I shake the lid a bit and a letter falls out.

It’s been scribbled hastily on a piece of loose-leaf paper, and the handwriting is hardly legible. It’s not from Hopeless, but it’ll have to do. I sigh and begin to read.

_Dear ~~Ms.~~ Miss Everything,_

_What does it mean when someone who has always been an arse to you starts acting weirdly nice? My ~~sworn enemy~~ arsehole roommate has been really civil and even nice to me lately, and I don’t really know what to do. How do I know if he’s just plotting against me?_

_From,_

_~~S~~ Confused_

_P.S. Can you leave your answer in the library between ~~Shakespareian~~ Shakespearian Spells Volume 2 and Volume 3? Thanks!_

I have to admit, I wasn’t expecting this. Obviously I start to jump to conclusions that maybe this is Hopeless’ person-of-interest, but I’m getting ahead of myself. Confused and Hopeless could be writing about completely separate events. I shouldn’t let my optimism get out of control.

_Dear Confused,_

_People don’t usually act nice as a way of trying to harm others. If you are really curious you should try being nice back! If they’re usually hostile, it’s doubtful that they’ll expect you to respond positively to them being nice._

_Best of luck!_

_Miss Everything_

There! That is just vague enough to not be entirely suspect, but specific enough that Hopeless is bound to notice if my suspicions are correct.

This is going to be interesting.

**Notes for the Chapter:**

> Hi guys!! It's been a while since I've uploaded, I got caught up in life stuff and just lost all motivation and creative thought. Unfortunately I can't promise I'll have a regular upload schedule or be able to finish this fic at all but I can promise I'll try my best to.
> 
> As always thanks for reading and extra thanks to anyone who leaves comments or kudos, you guys are what keep me inspired!! <3 
> 
> Have a great day btw :))


	3. P.S. I'm hopeful

**Agatha**

This morning I opened the brass letter box to find two new messages:

_Dear Miss Everything,_

_I followed your advice, and I’m surprised to say it went well. In fact, it’s working a bit too well for comfort. It’s only been two weeks since I started being civil with them and they’ve been more than pleasant in return. They were suspicious at first, but they seemed to warm up to me very quickly. The change was so sudden I was caught off guard and may have accidentally been a bit too open with them._

_To be entirely honest, I don’t quite know where to go from here. Are we friends now? I don’t know if it was truly that easy. Please lend me some insight._

_Sincerely,_

_(Still) Hopeless_

_P.S. I’m fully aware I’m taking your advice at my own risk._

The first letter was the same as always, nice stationary, nondescript handwriting, red wax seal with an calligraphic “B” stamped into it.

Sometimes I wonder who Hopeless could be. I wonder if I know them, if maybe we could be friends. They seem so guarded at first, but it’s not too hard to find their soft side once you know where to look.

The second letter was far less formal. It was the same messy handwriting scribbled onto crumpled loose-leaf as last time.

_Dear Miss Everything,_

_You gave me some advice a while ago on how to deal with my roommate being suspiciously nice to me, and I’m asking for help again. I think I’ve become friends with him. At least I hope I have. This is much better than fighting._

_I don’t know what to do next. I think I’d like to be friends with him, if he keeps being nice to me. I’m still a bit cautious around him, a couple weeks of being nice can’t erase years of acting awful (not that it wasn’t mutual). What do you think? What should I do?_

_Thank you,_

_Confused_

_P.S. Please leave your answer in the same place as last time, between Shakespearian Spells Vol. 2 and 3._

I sigh and drop my face into my hands. I’m almost certain these letters are written about the same two people. It’s getting hard to track who’s said what. Maybe I should try that thing Penny taught Simon, making lists of what I know. I open my notebook and start writing.

_What I Know (if Hopeless and Confused are writing about each other)_

  1. _They’re roommates_



Confused introduced their unnamed person as their “arsehole roommate”. This would explain why they seem to interact with each other a lot.

  1. _They hate each other (or Confused thought they did)_



It’s pretty clear this feud was either one-sided or non-existent. If Hopeless and Confused are the same people, then Hopeless never actually hated Confused. Whether Confused ever hated Hopeless remains to be seen.

  1. _They both want to be friends with each other_



I know Hopeless says they have feelings for their unidentified person of interest, but they seem somewhat content to be friends with them at the very least.

_Dear Confused,_

_Talk to him! Exchange banter! Treat him like you would any of your other friends! If you’re really unsure whether you’ve befriended him, you can always ask them._

_Sincerely,_

_Miss Everything_

I sigh, stretching in my chair and yawning loudly. I roll a new sheet of paper into my typewriter.

_Dear Hopeless,_

_If the information you gave me is accurate, then I think it’s safe to say you’ve become friends with them! I know you’ve mentioned that you have romantic feelings for them, and so I feel obligated to suggest that you start subtly flirting with them. The operative word here is subtly. Don’t start laying it on too thick, you don’t want to scare them away._

_Best of luck,_

_Miss Everything_

_P.S. I’m hopeful._

**Notes for the Chapter:**

> Hellooooo everyone! Hope you're having a nice day/night!! :))  
> As always, thank you so much for reading (and extra thanks to everyone who leaves kudos and comments, you guys make my day)!  
> I'll be back with more soon, happy reading!! <3


	4. Confused Five Times Over

**Agatha**

Tonight’s correspondence has been, for lack of a better word, eventful. I opened my brass mailbox to not two, but seven letters. One of them came from Hopeless. One came from a writer named “Truly Fucked”. The remaining _five_ were from Confused.

_Dear Miss Everything,_

_I’d like to thank you for your assistance these past few days. I realize that this is likely the end of our correspondence (for better or for worse on my behalf). Your advice was surprisingly more helpful than I thought it would be. Perhaps writing to you was the right decision after all (although the verdict’s still out on that)._

_Thank you for all your helpful words. For my sake, I hope this is the last time you’ll be hearing from me._

_Sincerely,_

_Hopeless_

I’m almost sad to stop hearing from Hopeless. I definitely don’t consider them one of my friends (that would be absurd, I don’t even know them), but I enjoyed writing to them. I hope everything works out in the end. They seem like a genuinely nice person, even if they are a little uptight at times.

The five letters I received from Confused are… interesting. I managed to sort them into the order I believe they were sent in, but I’m nowhere near certain as to my accuracy.

_Dear Miss Everything,_

_I think I’ve managed to actually befriend him! It’s strange, but it’s actually really nice! Thank you for all your help! :)_

_Thanks again,_

_Confused_

That’s the least eventful of them all.

_Dear Miss Everything,_

_Alright, I know this sounds strange, but I think I might be attracted to my arsehole friend/roommate. I don’t know what to do! I don’t know what this means!_

_From,_

_Confused_

It doesn’t end there.

_Dear Miss Everything,_

_Okay- now I’m absolutely positive I’m attracted to him. Even worse, I think I might have feelings for him? This makes everything so much more complicated. I really don’t know what to do._

_Please help,_

_Confused_

It gets better.

_Dear Miss Everything,_

_Alright, I know I’m sending you a lot of letters (I promise I’ll stop soon), but I’m mildly panicking. Normally I would ask my best friend for advice, but I’m not sure I’m ready to talk to her about this (or anyone I know irl)._

_I have a crush on my roommate (who only stopped hating me a few days ago). I don’t know what I should do. I just managed to get on his good side- is making a move worth ~~jeapardizin~~ g jeopardizing that?_

_Sincerely,_

_Confused_

And last but not least…

_Dear Miss Everything,_

_It’s been a few hours since I sent my other letters. I’ve mostly been trying not to think about my roommate fiasco, but he makes it impossible. He’s everywhere. It’s like I can’t manage to avoid him! (Not that I want to, but I couldn’t if I tried.) I can’t even form a whole sentence around him (though that’s not a recent development…). To top it all off I’m not very good at hiding my feelings around him._

_I’ve tried not to make things awkward between us, but since I’ve realized my feelings I’ve failed miserably. It hasn’t even been a whole day, and we’ve already fought twice. He stormed out during our last argument and I feel awful._

_I don’t know what I should do. I really don’t think I’ve got a chance with him. I know that doing nothing will only make it harder for me to move on, but I’m afraid that telling him how I feel will ruin what we already have._

_Please give me some advice,_

_Confused_

_P.S. Don’t worry, this is the last letter for now!_

I rub my temples in circular motions. Just when I thought it couldn’t get more complicated…

I pull out my notebook and review my list of information.

  1. _~~They’re roommates~~_ _They might be roommates_ ~~~~
  2. _~~They hate each other (or Confused thought they did)~~_ _IF they are roommates, they hate each other (or Confused thought they did)_ ~~~~
  3. _~~They both want to be friends with each other~~_ _IF they are the same people, then they want to be friends with each other_ ~~~~



I add the new developments to the list.

  1. _Hopeless has feelings for someone_
  2. _Confused has feelings for their roommate_
  3. _Neither of them think confessing their feelings is a good idea_



I rest my head in my hands as I slouch against the back of the hard library chair. If these two are in fact writing about each other, then this is simultaneously adorable and incredibly frustrating. This rivalry turned romance might just be the death of me. It almost reminds me of-

“Hi Agatha,” Penny interrupts my train of thought as she sits down in the chair across from me.

“Oh. Hello Penny,” I sigh as I hurriedly shove the letters into my purse. “How are you?”

“Er, a bit worried, if I’m being honest.” She says hesitantly.

“Why’s that?”

“Well it’s just… have you noticed anything strange going on with Simon and Baz lately?” She continues and I sigh inwardly. It’s pretty typical of Penny to only talk to me about Simon.

“I can’t say,” I tug on the sleeve of my jumper. “I haven’t really spoken to either of them recently.”

“Do you think maybe they’re…,” Penny trails off before shaking her head. “Sorry, never mind, I’m overthinking things.”

I yawn slightly, realizing it’s getting late. I should really write back to Confused before I fall asleep.

“Sorry, Penny, but I have to go,” I stand but she hardly takes notice. She’s staring at something across the library.

“Look at them…,” She mutters.

I turn to see what she’s talking about and find myself looking at Simon walking quickly after Baz, who either doesn’t know Simon is chasing after him, or is ignoring him on purpose. I roll my eyes. That’s nothing to take notice of- that’s exactly how they’ve always been. 

“Goodnight Penny,” I push in my chair and head for the exit as Penny bids me goodnight in return.

When I get back to my room, I settle down at my desk.

_Dear Confused,_

_The first thing you should do is make things right with him. Apologize for fighting- even if it isn’t your fault. Most people who won’t apologize first after a fight are just too stubborn to admit they’re wrong._

_Second of all, it is of my own personal opinion that you should tell him how you feel. However, I don’t want you to feel pressured into doing it just because I am of the opinion that you should. It is your decision, and you shouldn’t let my reading of such a vaguely described situation affect your actions one way or the other. I really think you have more of a shot than you give yourself credit for- maybe now is a time to be a little brave and cross that line!_

_I hope that whatever you do turns out for the best._

_Best of luck to you,_

_Miss Everything_

**Notes for the Chapter:**

> Hello! Oops- It's been a while! Sorry it took me so long to update this- I actually wrote the last two chapters back in December, but I suffered a major data loss and had to start over from scratch. (Don't worry, i think I wrote them better the second time anyway.) Chapter 5 will be going up tomorrow.
> 
> Thank you all so much for reading and I'm sorry about the major delay in updates! 
> 
> Extra thank you to anyone who leaves kudos and comments, you guys are the best!! :)))


	5. (Formerly) Hopeless and Confused

**Agatha**

I left the letter between Shakespearian Spells Volumes 2 and 3 this morning after breakfast. I hope everything works out for both Confused and Hopeless, even if they were completely separate people all along. Maybe I’ll hear from Confused again, but somehow it doesn’t feel like it. This time the response feels very final.

I wonder if I’ll ever get any letters this interesting with permission to publish them. It would certainly get my column loads more attention if I did.

Maybe someday.

* * *

It’s been a few days since the Hopeless/Confused conundrum ended. In a way it’s a lot more relaxing, but I miss having something interesting (and not life threatening) to think about.

I’ve taken to eating with Penny and Simon again. It was a little awkward at first, but we all got over it pretty fast. It’s nice to be able to hang out with the three of us again. If I’m being honest, I did miss it a little bit.

It’s halfway through dinner, with Simon nowhere to be seen, when a sudden hush falls over the dining hall. Penny drops her fork mid-bite, and I quickly turn to see what everyone is gaping at.

Simon and Baz walk towards our table, hand in hand. Baz looks as nonchalant and bored as ever, but Simon’s grinning from ear to ear. I purse my lips in an effort to keep my jaw from dropping, though I’m positive my shock is still written all over my face.

“Bunce, Wellbelove.” Baz says in greeting before kissing Simon on the cheek and walking away, evidently to get food for the both of them.

“Hi, Pen. Hi, Ags.” Simon blushes as he sits down, not meeting our eyes.

“Simon Snow!” Penny scolds. “I cannot believe you! When were you planning on telling us about that?”

“Er, now?” He smiles sheepishly, turning an even brighter shade of red.

Penny shakes her head and smiles at him.

“I’m happy for you, Simon. I saw it coming from a mile away, but I’m happy for you nonetheless.”

“Me too,” I add honestly. “I can’t say I saw it coming, but as long as you’re happy, I’m happy for you.”

“Thanks, you guys,” Simon beams at both of us. “And I am. Happy. I’m really, _really_ happy.”

Penny starts trying to pry details out of Simon, but he evades her questions (not all that smoothly, but that’s Simon for you).

“Bunce, give my boyfriend a rest, will you?” Baz groans when he returns with his and Simon’s food.

Eventually Penny and Baz launch into an argument about philosophy or ethics or something (I stopped paying attention). Simon’s eating and staring at Baz with a dreamy look on his face. I work on an elocutions essay, ignoring the lot of them to the best of my ability.

* * *

I sigh as I check the little brass mailbox. I’m not actually expecting a response this time, but it was nice while it lasted.

To my surprise a single gold embossed envelope falls into my hand. I trace the red wax seal on the back. I’m starting to get déjà vu.

I start walking back to the Cloisters, passing through the courtyard as I peel back the seal and open the envelope. I pull out the stationary and read.

_Dear Miss Everything,_

_Thank you. You really do give good advice._

_Sincerely,_

_(Formerly) Hopeless and Confused_

I smile, folding the letter neatly and sliding it into my coat pocket.

I stop short as the light from the top of Mummer’s Tower catches my eye. Finally, the penny drops.

I shake my head, still smiling. No wonder their handwriting looked so familiar.

**Notes for the Chapter:**

> Hi!! Hope everyone is doing well! :) 
> 
> Here's the final update, as promised. I really enjoyed writing this fic, to be honest it might be one of my favorites I've ever written (not that that says much lmao). I may or may not be planning a Dev/Niall follow up fic (I hinted at it in chapter 4, oops). 
> 
> Once again, thank you all so much for reading, I really hope you enjoyed it! Extra thanks to everyone who leaves comments and kudos, you guys are seriously the best! :)) <3
> 
> (I have a list of fics that I'm either planning on writing or working on currently, however if anyone wants me to try a certain trope/AU I am more than open to suggestions!)
> 
> Hope to see you soon! <3

**Author's Note:**

> I don't own any of these characters, this is just a fan-made parody work :)


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